Benzaldehyde → N-BENZYL-L-SERINE, METHYL ESTER

HRID 1864485Notes

Reaction equation

HRID 1864485 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:9])[C@H:5]([CH2:7][OH:8])[NH2:6].C(N(CC)CC)C.[CH:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[O-]S([O-])(=O)=O.[Mg+2].[BH4-].[Na+]>C(Cl)Cl>[CH3:2][O:3][C:4](=[O:9])[C@H:5]([CH2:7][OH:8])[NH:6][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 5

HCID 240BenzaldehydeHCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 2723730L-Serine, methyl ester, hydrochloride (1:1)HCID 4311764Sodium borohydride

Product 1

HCID 11790456N-BENZYL-L-SERINE, METHYL ESTER

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of serine methyl ester hydrochloride (3.0 g, 19.28 mmol) and triethylamine (2.7 mL, 19.28 mmol) in methylene chloride (30 mL) was added benzaldehyde (1 equivalent), followed by 2 g anhydrous MgSO4. The mixture was stirred at room temperature in a sealed flask for 20 hours, and then the solids were filtered away, and the filtrate was evaporated. The residue was redissolved in methanol (50 mL), and sodium borohydride (1 equivalent) was carefully added. The mixture was stirred for 30 minutes, was diluted with methylene chloride, was washed with NaHCO3, and was then dried over magnesium sulfate. The desired title product was obtained as a yellow oil and was used crude. N-4-methoxybenzyl serine methyl ester was made in a similar fashion using anisaldehyde in place of benzaldehyde.

Workup

  1. filtrationthe solids were filtered away
  2. customthe filtrate was evaporated
  3. dissolutionThe residue was redissolved in methanol (50 mL)
  4. stirringThe mixture was stirred for 30 minutes
  5. washwas washed with NaHCO3
  6. dry with materialwas then dried over magnesium sulfate

Sources & evidence

ORD record
ord-2068fef184444b4d809813eea03fb5f4
Source dataset
uspto-grants-2009_12
Patent number
US07625909B2

Reaction notes

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